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$1,800,000
6 Beds ⋅ 6 Baths ⋅ 1004553 MLS
Set behind black iron gates and approached by a long sweeping driveway, this extraordinary all-brick estate is a rare offering rich in history, character, and timeless elegance. Originally built in 1905 and set on 8.95 picturesque acres along the scenic Nissequogue River, this landmark property captures the grandeur and old-world appeal of a bygone era while offering an incredible opportunity to restore and reimagine a truly special home. In addition to the main parcel, the property also includes an additional 4.5 acres of wetlands located across the river, creating an exceptionally rare and expansive setting. Steeped in history, the residence once served as a hunting and fishing lodge in the early 1900s and showcases exquisite architectural detailing and craftsmanship rarely found today. Once owned by famed actress Dina Merrill, the estate carries with it a remarkable sense of legacy and prestige. From the moment you enter, the home is filled with warmth and character, featuring impressive millwork, rich wood floors, spacious formal entertaining rooms, and elegant period details throughout. At the heart of the home is the magnificent grand ballroom with soaring ceilings and a stunning stone fireplace — an unforgettable space reminiscent of the estate’s storied past and ideal for grand entertaining. The residence also features a desirable first-floor primary bedroom suite, generously sized rooms throughout, a full basement, and a expansive detached garage. Surrounded by natural beauty and offering exceptional privacy, this remarkable property presents endless potential for those who appreciate historic homes and old-world elegance. Conveniently located just minutes from Long Island beaches, restaurants, shopping, and the LIRR. A truly rare and iconic North Shore estate waiting to be restored to its former glory. Offered in “as is” condition. Please note: Listing photographs reflect the home at the time the current owners purchased the property and do not represent the current interior contents. All contents will be removed prior to closing.

274 River Road, Saint James
$1,599,999
6 Beds ⋅ 5 Baths ⋅ 1021330 MLS
Nestled on over 2 private, level acres in the prestigious Village of Nissequogue, this beautifully maintained center hall Colonial offers 6 bedrooms, 4.5 baths, and an exceptional layout designed for comfortable living and entertaining. A grand entry foyer welcomes you into a home featuring soaring cathedral ceilings, spacious living areas, and a spectacular 20.6' x 30' kitchen with abundant cabinetry and workspace that serves as the heart of the home. The oversized formal dining room is ideal for hosting gatherings, while the versatile floor plan includes two primary suites on the main level and a third primary ensuite upstairs, along with three additional generously sized bedrooms and another full bath. Step outside to your private backyard retreat featuring a heated in-ground pool surrounded by mature landscaping. Additional highlights include a two-car garage, beach access, mooring rights, and an exceptional North Shore location offering privacy, tranquility, and estate-style living.

15 Stillwater Road, Saint James
$1,599,990
5 Beds ⋅ 5 Baths ⋅ 1038556 MLS
Rare offering in Mills Pond Estates. Situated in a quiet cul de sac sits this beautifully maintained post modern gem. Soaring entry foyer, Formal living room with vaulted ceilings, banquet dining room, custom gourmet kitchen with custom cabinetry, granite counters, sub-zero refrigerator, Dacor double over and gas range, two dishwashers, wine bar with sink and wine refrigerator and large center island and spacious dining area. The kitchen flows into a cozy family room with wood burning fireplace/wood stove... countless memories will be made in this beautiful, flowing ,open living space. The first floor affords a fifth bedroom or, as currently used, a custom built and designed office space with desks and cabinetry and full bath. Office leads to the back yard making the space ideal for guests or nanny or a quick rinse after a dip in the pool. Enjoy your primary suite with amble closet space and newer beautifully tiled bath with walk in shower, soaking tub, dual vanity, radiant heat floors, towel warming bar and state of the art commode. Three additional spacious bedrooms and newer full bath with similar features.. beautiful tile, radiant heat floors, heated towel bar and state of the art commode. The home affords you all of the amenities you would expect. Efficient gas heat ( new in 2024) Newer roof (2023), Andersen windows, CAC, IGS, CVAC, Surround Sound and lighting controlled from your phone, Extensive hardscaping, patios and outdoor kitchen with gas BBQ... Lazy mountain lake salt water pool with new liner and new gas heater... to much to list and must be seen! All this in the desired and sought after Hamlet of St. James with it's neighborly Lake Ave and restaurant row on 25A.... Visit Avalon, The St. James General Store, local North Shore Beaches, Kayak the Nissequogue River.. take a short ride to Stony Brook Village with its shops, restaurants, museums and the Jazz Loft or the New England like harbor front Port Jefferson Village with it's ferry to New England.. The North Shore affords you the best in health care with Stony Brook Hospital, St. Catherine's, Mather Hospital and St. Charles hospital all a short car ride away. Stony Brook University also offers an array of activities from athletics events to events and shows at the Staller and Wang Center. Hop on the LIRR and in no time you're in the most exciting city in the world! Did we mention the acclaimed Smithtown School District. A lifetime of memories will be made in this home. It's why Mills Pond Estates homes rarely come up for sale.

5 Kenwood Lane, Saint James
$1,399,000
5 Beds ⋅ 5 Baths ⋅ 991522 MLS
Welcome to 138 Cambon Avenue: A Masterpiece of Custom Luxury and Efficiency Nestled in the heart of St. James, this custom-designed 5-bedroom, 3 Full / 2 Half bathroom residence at 138 Cambon Avenue offers a rare "move-in and unpack" opportunity, perfectly blending luxury with modern efficiency at $1,399,000. The grand interior features soaring high ceilings, efficient gas heat, central air conditioning, and a stunning designer kitchen equipped with premium granite countertops, a built-in espresso machine, and a specialized slow cooker steamer. The home's layout is uniquely versatile, boasting a fully finished basement with a separate entrance, kitchen, and bedroom—creating potential for a mother-daughter setup or accessory apartment with proper permits. A major financial asset to this property is the fully owned solar panel system, which ensures exceptionally low utility costs. Each bathroom has been reimagined with a modern, spa-inspired aesthetic, while the five spacious bedrooms provide ample room for all. The exterior is a true private oasis, meticulously finished with new pavers and professional masonry, featuring a full outdoor kitchen for premier entertaining and a detached three-car garage. Experience a resort-style lifestyle in this masterfully crafted home that balances high-end custom finishes with significant long-term energy savings.

138 Cambon Avenue, Saint James
$1,190,000
5 Beds ⋅ 3 Baths ⋅ 1032455 MLS
Located on a picturesque, tree-lined street in the heart of St. James, this stunner checks every box! Flooded with sunlight, the spacious kitchen features custom white cabinetry, a large center island and stainless steel appliances and opens seamlessly into a large den with fireplace. The expansive living space overlooks the private, resort-like yard. The two-story entry foyer, coupled with the 9 foot ceilings on the entire first floor and the tray ceiling in dining room enhance the bright and airy feel of this entertainers dream. All of the principle rooms are large and there are hardwood floors throughout. The oversized primary suite has a tray ceiling, walk-in closet and a double vanity spa-like en-suite bath with soaking tub. Additional bedrooms are all well-sized with excellent closet space, and a fifth bedroom with full bath on main level is ideal for home office or guest suite. Outside, an in-ground heated, saltwater pool is complimented by a serene waterfall feature and has a large paver patio perfect for abundant seating, lounging and entertaining. The full basement offers high ceilings. Generator panel in garage and portable generator that stays with the home. Plus, 200 amp service provides added peace of mind. Updated CAC, Andersen windows. In-ground sprinklers. This home will not last!

61 Hillside Avenue, Saint James
$1,099,000
4 Beds ⋅ 3 Baths ⋅ 936585 MLS
Why settle for someone else’s dream when you can build your own? Welcome to this brand-new TO BE BUILT colonial-style home designed with today’s lifestyle in mind. Set on a deep 15,840 sqft lot, this to-be-built beauty will offer over 2,400 square feet of fresh, functional living space and the kind of craftsmanship and energy efficiency only new construction can deliver. Inside, you’ll find four bedrooms, including a spacious primary suite with a walk-in closet and private bath, plus two additional full bathrooms—plenty of space for guests, or a growing household. The open-concept kitchen will shine with granite countertops, stainless steel appliances, and flows right into the formal dining room for easy entertaining. This home will be built with Energy Star-rated systems, a separate hot-water storage tank, and high-quality materials throughout. You’ll also get a full basement with customization potential and a scenic south-facing backyard that’s perfect for relaxing or creating your own outdoor retreat. Located in the Smithtown School District and close to parks, shopping, and transportation—it checks every box for modern living. Now’s the time to secure your future in a brand-new, energy-efficient home in a prime Long Island location. Ask about our Builder Incentives

120 4th Street, Saint James
$1,099,000
4 Beds ⋅ 3 Baths ⋅ 936825 MLS
Why settle for someone else’s dream when you can build your own? Welcome to this brand-new TO BE BUILT colonial-style home designed with today’s lifestyle in mind. Set on a deep 15,840 sqft lot, this to-be-built beauty will offer over 2,400 square feet of fresh, functional living space and the kind of craftsmanship and energy efficiency only new construction can deliver. Inside, you’ll find four bedrooms, including a spacious primary suite with a walk-in closet and private bath, plus two additional full bathrooms—plenty of space for guests, or a growing household. The open-concept kitchen will shine with granite countertops, stainless steel appliances, and flows right into the formal dining room for easy entertaining. This home will be built with Energy Star-rated systems, a separate hot-water storage tank, and high-quality materials throughout. You’ll also get a full basement with customization potential and a scenic south-facing backyard that’s perfect for relaxing or creating your own outdoor retreat. Located in the Smithtown School District and close to parks, shopping, and transportation—it checks every box for modern living. Now’s the time to secure your future in a brand-new, energy-efficient home in a prime Long Island location. Ask about our Builder Incentives

122 4th Street, Saint James
$1,095,000
4 Beds ⋅ 3 Baths ⋅ 1001456 MLS
Set on .61 acres of flat, beautifully landscaped property in the Hamlet of St. James, this well maintained center-hall Colonial combines timeless charm with spacious living and thoughtful recent updates throughout. The formal living room, dining room, and oversized den are filled with warmth and character, featuring wide-plank pine flooring and generous entertaining space. The den is anchored by a charming wood-burning fireplace, creating the perfect setting for cozy evenings and gatherings. The sun-filled kitchen offers oak cabinetry and is centered around a large island, with a bright breakfast area and sliding doors that open to the backyard oasis. The spacious primary suite provides a peaceful retreat with a walk-in closet and a recently renovated spa-like bath featuring an oversized shower and double-sink vanity. Three additional bedrooms offer wall-to-wall carpeting over hardwood flooring and include custom closet systems. Additional highlights include a large unfinished basement ideal for storage or future finishing, recent updates to the roof, central air conditioning, and bathrooms, offering comfort and peace of mind for years to come. Step outside to your private fully fenced resort-style backyard, complete with an inground saltwater pool with new salt system and paver patio perfect for summer entertaining, relaxing weekends, and outdoor living at its finest. Nearby is local shopping, area beaches, fine dining, and Stony Brook University and Medical Center. Smithtown Schools.

41 Astor Avenue, Saint James
$1,050,000
4 Beds ⋅ 3 Baths ⋅ 1023141 MLS
Welcome to this beautifully maintained 3,068 sq. ft. Colonial set on a private .91-acre property in the prestigious Village of Head of the Harbor within the Smithtown School District. This spacious home offers 4 bedrooms, 2.5 baths, a finished basement, and a 2-car garage. The inviting floor plan features a formal living room, formal dining room, family room, and bonus room perfect for a home office or playroom. Hardwood floors run throughout the home, complemented by two beautiful wood-burning fireplaces and a full-length attic for exceptional storage. The cherry and granite kitchen features updated appliances, while the renovated bathrooms offer granite double vanities and custom flooring. Recent updates include a new heating system and central air (2022), brand new hot water heater, 200-amp electric, roof (2021), and Andersen windows, including dormers, replaced in 2021. Exterior highlights include cedar siding, a charming front portico, wood deck, bluestone patio, wood fencing, gazebo, and a 10-zone in-ground sprinkler system. The expansive backyard offers plenty of room for entertaining or a future pool. This is a rare opportunity to own a spacious, move-in-ready Colonial in the prestigious Village of Head of the Harbor, offering classic character, quality updates, exceptional privacy, and an unbeatable North Shore location.

9 Three Sisters Road, Saint James
$999,999
3 Beds ⋅ 3 Baths ⋅ 1010352 MLS
Set on over half an acre at the end of a quiet Saint James cul-de-sac, this 4 bedroom, 2.5 bath, 3,313 square foot newer construction center hall colonial offers space, flexibility, and a layout that works for the way people actually live. Hardwood floors run throughout the home, starting with a traditional first-floor layout that includes a welcoming foyer, large formal living room, formal dining room, and a comfortable family room with a wood burning fireplace. Off the family room, sliders open to a huge three-season (300 sq ft) room, creating an additional space to relax, gather, or enjoy the view of the property. From there, another set of doors leads outside, giving the home an easy connection between indoor living and the backyard. The eat-in kitchen anchors the main level with a large center island, generous prep space, sliders to the backyard, and a small butler’s pantry connecting the kitchen and dining room. A first-floor laundry room, two-car attached garage, and basement access add function and convenience to the main level. Upstairs, the second floor opens to a beautiful view overlooking the formal living room below, where cathedral ceilings add height and character to the home. The spacious primary bedroom features vaulted ceilings, two large closets, and an oversized primary bath, while the additional bedrooms feel bright and comfortable with large windows that bring in great natural light. The current upstairs setup offers 3 bedrooms, but this level was originally designed as a 4-bedroom layout and can easily be converted back with one simple wall. With generous room sizes and a flexible second-floor layout, the space can adapt to different needs while still keeping an open, connected feel throughout the home. Outside, the .58-acre property offers a private backyard setting with an in-ground pool, paver areas for lounging and entertaining, in-ground sprinklers, and landscaped front and rear grounds. There is room to enjoy the yard in different ways, whether you are hosting, relaxing, or just appreciating having extra space around you. With its cul-de-sac location, generous square footage, newer construction, and flexible layout throughout, this Saint James colonial offers the kind of space that can grow and change with you.

11 Annemarie Drive, Saint James
$999,900
4 Beds ⋅ 3 Baths ⋅ 966893 MLS
Huge Price Reduction — Opportunity of a Lifetime! Set on 1.25 beautifully maintained, level acres within the highly desirable community of St. James, this exceptional property offers the perfect balance of space, privacy, and versatility — with a rare equestrian component that elevates it beyond the ordinary! The impeccably maintained Center Hall Colonial features 4 bedrooms and 2.5 baths with a gracious, flowing floor plan designed for both comfortable everyday living and effortless entertaining. Rich wood floors run throughout the home, complemented by tasteful neutral decor and abundant natural light. The custom updated eat-in kitchen is thoughtfully appointed with stainless steel appliances, granite countertops, and a charming dinette area overlooking the expansive property — creating a seamless indoor-outdoor connection. Formal living and dining rooms provide an elegant gathering space, while the warm and inviting den has a wood burning fireplace and offers a cozy retreat. The primary bedroom features a private ensuite bath, and three additional generously sized bedrooms complete the second level. Updated windows and bathrooms, central air conditioning, a full finished basement with outside entry, and a two-car garage enhance everyday convenience. Additional improvements include low-maintenance vinyl siding, and a generator transfer switch for added peace of mind. Pride of ownership is evident throughout. For those seeking additional flexibility, the property is thoughtfully equipped for equestrian use. A center aisle working barn includes four 12x10 matted breeding stalls, 50-amp electric service, water, heat and ventilation fans, loft exhaust system, and phone lines. Outdoor amenities feature a riding ring with lighting, sprinkler system for dust control, paddock and grazing areas, wash rack, and full secondary fencing. The grounds provide a private and versatile environment suitable for training, conditioning, or leisure riding — all within the comfort of your own property. Located within the Smithtown School District, this unique property is just minutes from shopping, restaurants, parks, transportation, Stony Brook University, Stony Brook Hospital, and the beaches of the Long Island Sound. Offering a rare combination of space, flexibility, and convenience, this exceptional St. James property presents an outstanding opportunity to create something truly special. Whether enjoyed as-is or tailored to suit your vision, this remarkable offering is ready for its next chapter. Must see to appreciate.

14 Hillside Avenue, Saint James
$995,000
4 Beds ⋅ 3 Baths ⋅ 1024831 MLS
This Yablonski Built Home is Located In The Village of Nissequogue and is Nice Center Hall Colonial with Some Renovations, (Kitchen) Done 5 years ago. The Foyer Floor is Original Parquet and the Banister Leading up The Stairs is Quite Impressive. There are 4 Large Bedrooms, Primary Has its Own En-Suite and a Walk In Closet. All Located on the second Floor. There is Also A Half Bath Up There as Well. A Large Kitchen with Tons of Storage and a Sit Down Island and The Perfect Banquet Bar with a Sink and Eating Area with a Fireplace, Where a Wall of Windows Fill The Room With Light. There is Also a Large Dining Room For Gatherings. The Extra Large Living Room Has Many Windows as Well, it Also Has a Window Seat For Curling Up and Reading a Book, Here is Where you Will Find Another Fireplace. To Top it Off The Original Hardwood Floors are Still in Perfect Condition. There is a Large Full Basement That is Unfinished That Can Be Accessed From Inside The Home and The Garage. There are 2 Acres To Do Whatever You Choose To Do. This Home is Located Right Across The Street From The 5th Hole of Nissequogue Golf Club.

11 Smith Lane, Saint James
$990,000
4 Beds ⋅ 3 Baths ⋅ 1028829 MLS
Welcome home to this Post Modern Colonial, where an impressive two-story entry foyer creates a grand first impression. Beautiful hardwood floors, finished in a modern gray tone, extend throughout the entry foyer, staircase, formal living room, and formal dining room, creating a warm and cohesive flow. Designed for today's lifestyle, the home features a desirable open-concept kitchen and family room with a wood-burning fireplace flanked by custom built-ins, making it the perfect gathering space. The spacious primary suite offers a walk-in closet and a private ensuite bath, while a conveniently located first-floor laundry/mudroom with a new front-load washer and dryer adds everyday functionality. Set on a landscaped .43-acre property in the heart of St. James, the private, fenced backyard is an entertainer's dream, featuring an expansive paver patio with a built-in firepit plus a separately fenced saltwater inground pool with waterfall. Pool updates include new filter, heat pump, and Loop-Loc cover, as well as new pavers surround the pool area, while the gazebo provides the perfect place to relax. Thoughtfully updated for today's modern lifestyle, the home features a Smart Home system allowing you to control lights, doors, and central air from your smartphone, along with a security system with cameras for added peace of mind. Additional improvements include a 2020 roof, a 2024 natural gas heating system, CAC with the second-floor compressor replaced in 2023, a separate gas hot water heater, 200-amp electric service with a dedicated panel for an EV charger, and owned solar panels installed in 2020, providing lower electric costs and valuable property tax exemptions. (Note: Taxes being professionally grieved with an estimated $3,300 reduction; grievance is transferable to the Buyer.) Ideally located on a cul-de-sac and just a short walk to Lake Avenue's shops and restaurants, including the new Galiano Wine Bar. This home also offers beach rights to multiple Town of Smithtown beaches, proximity to parks, hiking trails, and nature preserves, and is situated within the highly regarded Smithtown Central School District.

4 Patricks Way, Saint James
$899,000
4 Beds ⋅ 4 Baths ⋅ 1003970 MLS
Located on a pristine, tree-lined street north of 25A in highly desired St. James, this spacious 4 BR, 3.5BA colonial boasts hardwood floors throughout, 2 fireplaces, updated natural gas heat, and a full finished basement w OSE offering plenty of room for extended family. First floor offers a separate home office. The spacious 2 car garage has plenty of room for cars and additional storage. Updated Andersen windows, flat usable private yard with land-locked, state-owned property directly behind it, serving a beautiful, natural buffer for privacy. Central air approx 6 years old, 200 amp service, Cesspool is approx 10 years old. Roof approx 10 years old. Generously sized rooms and a primary en-suite with 2 closets and primary bath! This home offers an abundance of closet space and meticulously maintained In-ground sprinkler system. Short drive to beautiful north shore beaches and close to some of the most highly rated restaurants and shops in the area. Do not miss this opportunity!

3 Thompson Hill Road, Saint James
$899,000
4 Beds ⋅ 3 Baths ⋅ 995990 MLS
Incredible opportunity to be in Head of the Harbor in a sprawling farm ranch! Large principle rooms flow seamlessly in this sun-filled, private home. Picturesque, serene views can be seen out every window. The kitchen shares a double-sided fireplace with the living room, and the sunken den has its own additional fireplace. Two master en-suites, one on the main and on the second floor, give options for you to create a home that can meet all of your needs. Hardwood floors as shown and under carpet in all but 2 rooms. Andersen windows, updated baths, two car garage, basement. Taxes shown reflect both the town and village taxes. Great opportunity!

118 Harbor Road, Saint James
$839,000
5 Beds ⋅ 3 Baths ⋅ 1007352 MLS
The picture-perfect home with the white picket fence. Extensively renovated in 2022, this beautifully updated 5-bedroom, 2.5-bath residence blends charm with modern finishes throughout. Situated on a rare and expansive .67-acre property in the heart of St. James, the home features an open and inviting floor plan designed for both everyday living and entertaining. The main level offers a formal living room with fireplace, a spacious den with cathedral ceilings, and an open-concept kitchen and dining area. The kitchen is appointed with quartz countertops & custom cabinetry. Two bedrooms (possible first floor primary), full bath and a powder room complete the first floor, while the second level features three additional bedrooms and a renovated full bath. Nearly every aspect of the home was updated in 2022 & 2026, including the kitchen, bathrooms, windows, doors, siding, roof, fencing, mechanical systems, fixtures, and oil tank. The grounds offer exceptional outdoor space with expansive, level lawns, mature landscaping, a new paver patio, in-ground sprinkler system, and plenty of room for entertaining, recreation, or future enhancements. A detached two-car garage provides additional storage and convenience. A turnkey home offering the perfect combination of classic character, modern updates, and generous indoor and outdoor living spaces in a convenient St. James location. Will not last!

238 Woodlawn Avenue, Saint James
$839,000
3 Beds ⋅ 2 Baths ⋅ 999791 MLS
Elegant and inviting expanded ranch featuring numerous recent updates and spacious living throughout. Expanded in 2009, the home offers generously sized bedrooms and a layout designed for both comfortable living and entertaining Upon entering, you are welcomed by a spacious formal dining room highlighted by a large picture window that fills the space with natural light. Just beyond, the stunning great room features pegged hardwood flooring, a cozy wood-burning fireplace, and custom built-in bookshelves, creating the perfect gathering space. Recently remodeled in 2024, the kitchen boasts white cabinetry, quartz countertops, stainless steel appliances, and a sunny breakfast nook ideal for casual dining. The private primary suite offers a vaulted ceiling with high hats, a walk-in closet, and its own full bath. Two additional oversized bedrooms share a beautifully maintained full bathroom. Additional features include a partially finished basement, new central air conditioning, a new cesspool, updated heating system, and many new or replaced windows throughout the home. Outside, the fully fenced backyard creates a private retreat complete with an in-ground pool featuring a new liner and new heater — perfect for relaxing or entertaining all summer long. Ideally located near area shopping, fine dining, local beaches, and Stony Brook University and Medical Center. Smithtown Schools

28 King Arthurs Court, Saint James
$824,000
4 Beds ⋅ 2 Baths ⋅ 1023804 MLS
Welcome to this beautifully renovated Saint James home where no expense has been spared. Every detail has been thoughtfully updated, featuring board and batten siding, Andersen windows, and gorgeous hardwood floors throughout. The designer two tone kitchen showcases vanilla and warm brown shaker wood cabinetry, elegant granite countertops, and stainless steel appliances. Both brand new bathrooms have sleek, modern design. Additional upgrades include In ground sprinklers, brand new central air conditioning, new electrical panels for both the house and pool, and a fully finished basement with outside entrance. Step outside to your private backyard oasis featuring a newly updated in ground pool with brand new liner, pump, filter and beautifully landscaped grounds. Ideally located just minutes from Smith Heaven mall, shopping, dining, parks, and major roadways. This home offers both convenience and an exceptional lifestyle. Situated within the highly regarded Smithtown School District! This truly move in ready home delivers luxury finishes, quality craftsmanship, and incredible value. POTENTIAL MOTHER DAUGHTER SET UP AND BASEMENT WITH OUTSIDE ENTRANCE!

273 Cambon Avenue, Saint James
$819,000
4 Beds ⋅ 3 Baths ⋅ 887076 MLS
This unique property offers not one, but two separate dwellings on a beautifully half acre landscaped lot. The main residence is a well-maintained side-by-side split featuring 3 bedrooms, 2 full baths, hardwood floors, a cozy fireplace, and generous living space ideal for everyday comfort and entertaining. The second dwelling is a delightful 1–2 bedroom cottage complete with basement and attic and its own private yard and driveway—perfect for extended family, guests, or rental income opportunities. Enjoy outdoor living on the spacious back deck surrounded by mature trees, or unwind in the peaceful front yard on a dead end street. Whether you're looking for a multigenerational setup or an investment property, this versatile home is a rare find!

11 Grove Avenue, Saint James
$799,990
4 Beds ⋅ 3 Baths ⋅ 1035173 MLS
Lovely home with a beautiful front porch set in a cul de sac. Spacious rooms hardwood floors, and 9 ft ceilings throughout. The updated custom eat in kitchen has an open plan feels with beautiful cabinets quartz counters tops and Stainless appliances. There is a spacious eating area with patio doors leading to the deck.The large family room has a wood burning fireplace and is open to the kitchen. The primary bedroom is big with a tray ceiling walk in closet and ensuite bathroom. There are three addtional bedrooms and updated main bathroom. The laundry area is conviently located on the second floor. The basement is full with outside entrance.There is two zone central air which has been updated . Set on shy one acre of level parklike fenced property with a large deck

4 Fable Road, Saint James
$799,000
4 Beds ⋅ 3 Baths ⋅ 1014293 MLS
Welcome Home to this cozy, beautifully updated 4-bedroom, 2.5 Baths Colonial in the desirable community of Saint James. Featuring a wonderful open floor plan, this home is designed for comfortable everyday living and effortless entertaining. The updated kitchen offers warm wood cabinetry, quartz countertops, stainless steel appliances, and plenty of space for cooking and gathering. Hardwood floors flow throughout the home, adding warmth and character. Laundry and half bath off kitchen. The spacious primary bedroom features a private en-suite bath with a walk-in shower and large walk-in closet. Three additional good-sized bedrooms and a full hall bath. The basement, accessible through bilco doors, offers excellent storage space. Outside, enjoy a large, fully fenced-in backyard, perfect for entertaining, relaxing, or enjoying outdoor activities. A wonderful combination of comfort, style, and functionality in a great location close to all amenities.

136 Mills Pond Road, Saint James
$739,000
3 Beds ⋅ 2 Baths ⋅ 1028816 MLS
Welcome to this beautifully updated 3-bedroom, 2-bath home in the heart of St. James! Convenient distance to shops, restaurants and transportation with taxes under 9k! The stunning 2025 kitchen renovation is the centerpiece of the home. Showcasing natural quartzite countertops, full height backsplash, a 9 ft island with waterfall, professional grade appliances featuring a 6 burner gas range with vented hood. A bar area with beverage center and secondary workstation sink. Original hardwood floors run throughout the home. The fully enclosed, heated and air-conditioned front porch offers year-round enjoyment. The main level also features a formal living room, a full bathroom, recessed lighting, and efficient 4-zone heating and 3-zone cooling for personalized comfort. Upstairs, you'll find the three bedrooms, and another full bathroom, served by 3-zone heating and 2-zone cooling. The partially finished basement was completed in 2024 and provides additional living space. It has its own dedicated heating and cooling zone, along with a front-loading washer and gas dryer. A new high-efficiency Laars wall-mounted gas boiler was installed in 2025. In 2026, the home was fully insulated and finished with maintenance-free Cedar Impressions vinyl siding. The oversized detached two-car garage is equipped with a 60-amp subpanel, multiple 20-amp outlets, and hot and cold water with waste plumbing—ideal for a workshop or hobby space. The property also features a beautifully designed paver patio complete with a wet bar (2024)—perfect for entertaining, ample driveway parking, RV parking, hot and cold exterior water spigots. Additional highlights include Andersen® Thermopane windows, newer architectural roof, new exterior doors, 200-amp electrical service with generator hookup, wifi smart thermostats & porch lights, and eight surveillance cameras. Ideally located a short walk to Lake Avenues shop and restaurants. This home also offers beach rights to multiple Smithtown beaches, close proximity to parks, hiking trails and nature preserves. Situated in the highly regarded Smithtown Central School District.

116 Railroad Avenue, Saint James
$725,000
3 Beds ⋅ 2 Baths ⋅ 1026215 MLS
Nestled on an expansive 12,195 sq. ft. fully fenced property in the heart of St. James and located within the highly acclaimed Smithtown School District, this beautifully maintained farmhouse style Cape Cod is the perfect place to call home. Offering 3 spacious bedrooms and 2 full bathrooms, this inviting residence blends timeless charm with thoughtful updates throughout. Beautifully refinished hardwood floors, a sun filled living room with recessed lighting, a formal dining room, and an updated kitchen create a warm and welcoming atmosphere that's ideal for both everyday living and entertaining. Main-floor laundry adds everyday convenience. The second-floor features three generously sized bedrooms, a full bathroom, a huge walk-in closet, and a large walk-up attic, providing exceptional storage and flexibility. A full basement offers even more storage space and endless possibilities. Step outside to enjoy your private fully fenced front and backyard, complete with a newly updated patio perfect for summer barbecues, outdoor gatherings, gardening, or simply relaxing while enjoying the oversized yard. Ideally located just minutes from the St. James LIRR station, shopping, restaurants, parks, and major roadways, this exceptional home offers the perfect combination of charm, space, convenience, and location. Don't miss the opportunity to own this move-in-ready gem in one of Long Island's most sought-after communities.

214 1st Street, Saint James
$699,999
3 Beds ⋅ 2 Baths ⋅ 1006934 MLS
Welcome to 3 Bayberry Drive in the heart of Saint James! This beautifully updated home has been renovated from top to bottom within the last six years and offers the perfect blend of style, comfort, and functionality. The stunning kitchen, renovated in 2022, features quartz countertops, stainless steel appliances, custom tile backsplash, recessed lighting, glass display cabinetry, and thoughtful designer finishes throughout. The main bathroom was also completely updated in 2022. There is a full basement with an outside entrance. For added convenience, washer and dryer hookups are available on both the main level and in the basement. Additional updates include beautifully refinished hardwood floors on the main level (2022), central air conditioning on the main floor, and ductless split units in the basement for year-round comfort. Step outside to enjoy the private backyard retreat featuring a spacious deck leading to a large patio—perfect for entertaining guests, outdoor dining, or simply relaxing after a long day. Nestled in a picturesque, storybook neighborhood, this home offers a prime Saint James location close to everything the community has to offer. With countless updates and amenities throughout, this is truly a home that must be seen to be appreciated. Schedule your private showing today before this exceptional opportunity is gone!

3 Bayberry Drive, Saint James
$699,990
3 Beds ⋅ 3 Baths ⋅ 997288 MLS
This Colonial home features three bedrooms, 2 1/2 baths, eat in kitchen, formal dining room, large living room, family room with fireplace, basement, two car garage, large fenced yard - on a Dead End Street!

43 Vanderbilt Avenue, Saint James
$699,990
4 Beds ⋅ 3 Baths ⋅ 988297 MLS
Possible Mother Daughter with proper permits! The home is a split level with three bedrooms up and bath*main level has a large sunny living room, dining room and kitchen with energy star appliances and an office/studio apartment. There is a basement for great storage with new boiler and hot water heater. There is an oversized two car garage and a beautiful large yard with a new deck off the sliders of the dining room. Endless Possibilites!

67 Cleremont Avenue, Saint James
$685,000
3 Beds ⋅ 2 Baths ⋅ 1020879 MLS
Opportunity awaits in the heart of Saint James! This 4-bedroom, 1.5-bath home offers timeless character and incredible potential. Built in 1900 and in original condition, it's ready for your vision and updates. This historic property also features an oversized detached 3-car garage and a spacious workshop—ideal for hobbyists, contractors, car enthusiasts, or additional storage. Situated on a generous lot in a desirable location close to shopping, restaurants, parks, and transportation, this is a rare chance to restore a classic home and make it your own. Adjacent .13 acre lot included in the sale.

174 Railroad Avenue, Saint James
$678,000
4 Beds ⋅ 3 Baths ⋅ 1031653 MLS
Classic Colonial home offering spacious, and comfortable living . The expansive living room and beautiful wood floors throughout the home create a warm and inviting atmosphere. The eat-in kitchen flows seamlessly into the den, featuring a cozy wood-burning fireplace—perfect for everyday living and entertaining. The primary bedroom boasts an updated marble en-suite bath, while the additional bathrooms have also been tastefully renovated with quality finishes. In addition there are 3 nicely sized bedrooms on the second floor. The recently remodeled basement features durable luxury vinyl plank flooring and an outside entrance, providing versatile space for recreation, or a home office.. Step outside to enjoy the backyard deck with retractable awning, ideal for relaxing or hosting gatherings. Conveniently located near local shopping, the Long Island Rail Road, area beaches, fine dining, and Stony Brook University, and Stony Brook University Medical Center, this home offers the perfect combination of comfort, and accessibility. Smithtown Schools

322 2nd Avenue, Saint James
$655,000
2 Beds ⋅ 2 Baths ⋅ 1017062 MLS
Enjoy maintenance-free luxury in the highly desirable Fairfield at St. James community. This pristine 2-bedroom ranch condo is completely updated from top to bottom, featuring a stunning new kitchen, modern baths, and newer AC and hot water tank. With no one living above you and an attached 1-car garage, this home offers rare convenience and privacy. The back patio opens to peaceful views with total rear privacy. A turnkey gem that is an absolute must-see! Community amenities galore!

210 Elton Court W, Saint James
$649,000
3 Beds ⋅ 2 Baths ⋅ 1037603 MLS
.Welcome to 248 6th Avenue, a warm and inviting three-bedroom, two-full-bath ranch set on a beautiful, level 100 x 100 corner property in the Saint James Park section of St. James. Lovingly cared for by its longtime owner, this home feels comfortable the moment you walk through the door. Hardwood floors run throughout the home, while a large picture window fills the living room with natural light. The living and dining areas flow nicely into the updated kitchen featuring granite countertops, wood cabinetry, stainless steel appliances, gas propane cooking, recessed lighting, and a breakfast bar that's perfect for morning coffee or casual meals. Sliding doors lead to the deck and fenced backyard, creating an easy space for summer barbecues, entertaining, gardening, or simply relaxing outside. All three bedrooms feature hardwood floors, and the primary bedroom includes a double closet and private full bath. A full basement offers plenty of storage, plus great potential for a home gym, workshop, recreation area, or additional living space. Add in the attached garage, pull-down attic storage, and generous driveway, and there's room for just about everything. Conveniently located near Lake Avenue, the St. James LIRR station, local shops, restaurants, parks, and North Shore destinations. If you've been looking for comfortable one-level living with a great yard and a true neighborhood feel, 248 6th Avenue is ready to welcome you home.

248 6th Avenue, Saint James

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